Semi-synthesis of N-substituted Mahanimbine via Alkylation


  • Nurliana Mohd Yunos Department of Chemistry, Faculty of Science, Universiti Putra Malaysia, 43400 UPM Serdang, Selangor, Malaysia
  • Siti Mariam Mohd Nor Department of Chemistry, Faculty of Science, Universiti Putra Malaysia, 43400 UPM Serdang, Selangor, Malaysia
  • Mohd Azlan Nafiah Department of Chemistry, Faculty of Science and Mathematics, Universiti Pendidikan Sultan Idris, 35900 Tanjong Malim, Perak, Malaysia



Mahanimbine, Alkylation, N-terminal, Derivative, Murraya


Mahanimbine, a prenylated carbazole found primarily in the Rutaceae family, has remarkable biological features such as anticancer, antidiabetic and antioxidant. Therefore, it is intriguing to tweak the mahanimbine structure with the aim of adding extra value to their activity. Three new derivatives were semi-synthesised by N-alkylation of naturally isolated mahanimbine using alkyl bromides, yielding N-butylmahanimbine, N-(3-methylbutyl) mahanimbine, and N-benzylmahanimbine. The structures of N-alkylated mahanimbines were elucidated using different spectroscopic techniques (FTIR, GCMS, and NMR).


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Ahmad K, Tan S, Sukari M, Ali A, Nafiah M. (2014). Cytotoxic and anti-tumour promoting activities of carbazole alkaloids from Malayan Murraya koenigii (L.) Spreng. American Journal of Plant Sciences, 5, 2869-2877.

Bashir M, Bano A, Ijaz AS, Chaudhary BA. (2015). Recent developments and biological activities of N-substituted carbazole derivatives: a review. Molecules, 20(8), 13496-13517.

Bhattacharyya P, Roy S, Biswas A, Bhattacharyya L, Chakraborty DP. (1978). Mahanimbine and murrayazoline from Murraya exotica Linn. (Syn. Murraya paniculata). Journal of the Indian Chemical Society, 308-308.

Birari R, Javia V, Bhutani KK. (2010). Antiobesity and lipid lowering effects of Murraya koenigii (L.) spreng leaves extracts and mahanimbine on high fat diet induced obese rats. Fitoterapia, 81(8), 1129-1133.

Chakraborty M. (2020). Reactions of the carbazole alkaloid mahanimbine with mineral acid, Lewis acid and m-chloroperbenzoic acid. Indian Journal of Chemistry, 59, 837-841.

Chakraborty M. (2018). Nitration of C13, C18 and C23 carbazole alkaloids using ceric ammonium nitrate (CAN). Asian Journal of Research in Chemistry, 11(2), 337-343.

Chowdhury BK, Jha S, Bhattacharya P, Mukherjee J. (2001). Two new carbazole alkaloids form Murraya koenigii. Indian Journal of Chemistry, 40(6), 490-494.

Cuong NM, Hung TQ, Sung TV, Taylor WC. (2004). A new dimeric carbazole alkaloid from Glycosmis stenocarpa roots. Chemical and Pharmaceutical Bulletin, 52(10), 1175-1178.

Dahiya J, Singh J, Kumar A, Sharma A. (2016). Isolation, characterization and quantification of an anxiolytic constituent-mahanimbine, from Murraya koenigii Linn. Spreng leaves. Journal of Ethnopharmacology, 193, 706-711.

Dineshkumar B, Mitra A, Mahadevappa M. (2010). Antidiabetic and hypolipidemic effects of mahanimbine carbazole alkaloid from Murraya koenigii Rutaceae leaves. International Journal of Phytomedicine, 2, 22-30.

Hobani YH. (2022). Cytotoxicity of mahanimbine from curry leaves in human breast cancer cells (MCF-7) via mitochondrial apoptosis and anti-angiogenesis. Molecules, 27(3), 971.

Ito C, Katsuno S, Ohta H, Omura M, Kajiura I, Furukawa H. (1997). Constituents of Clausena excavate-isolation and structural elucidation of new carbazole alkaloids. Chemical and Pharmaceutical Bulletin, 45(1), 48-52.

Ito C, Itoigawa M, Nakao K, Murata T, Tsuboi M, Kaneda N, Furukawa H. (2006). Induction of apoptosis by carbazole alkaloids isolated from Murraya koenigii. Phytomedicine, 13(5), 359-365.

Joshi BS, Kamat VN, Gawad DH. (1970). On the structures of girinimbine, mahanimbine, isomahanimbine, koenimbidine and murrayacine. Tetrahedron, 26(5), 1475-1482.

Liu K, Zang Y, Shen C, Li C, Ma J, Yang J, Sun X, Chen X, Wang N, Zhang, D. (2021). Synthesis and biological evaluation of pyranocarbazole derivatives as anti-tumor agents. Bioorganic and Medicinal Chemistry Letters, 33, 127739.

Ma X, Chen H, Zhu S, Tu P, Jiang Y. (2021). Trimeric and dimeric carbazole alkaloids from Murraya microphylla. Molecules, 26, 5689.

Ma XL, Zhu SS, Liu Y, Chen HW, Shi YT, Zeng KW, Tu PF. (2021). Carbazole alkaloids with potential cytotoxic activities targeted on PCK2 protein from Murraya microphylla. Bioorganic Chemistry, 114, 105-113.

Mani V, Mohd Azahan NS, Ramasamy K, Lim SM, Abdul Majeed AB. (2021). Mahanimbine improved aging-related memory deficits in mice through enhanced cholinergic transmission and suppressed oxidative stress, amyloid levels, and neuroinflammation. Brain Science, 12(1), 12.

Meragelman KM, McKee TC, Boyd MR. (2000). Siamenol, a new carbazole alkaloid from Murraya siamensis. Journal of Natural Products, 63(3), 427-428.

Mohd Nor SM, Osman FNA, Ahmad K, Nafiah MA. (2017). Synthesis of N-alkylated and N-acylated derivatives of girinimbine. Asian Journal of Chemistry, 29(4), 801-804.

Mondal P, Natesh J, Abdul Salam AA, Meeran SM. (2022). Mahanimbine isolated from Murraya koenigii inhibits P-glycoprotein involved in lung cancer chemoresistance. Bioorganic Chemistry, 129, 106170.

Nakahara K, Trakoontivakorn G, Alzoreky NS, Ono H, Onishi-Kameyama M, Yoshida M. (2002). Antimutagenicity of some edible Thai plants, and a bioactive carbazole alkaloid, mahanine, isolated from Micromelum minutum. Journal of Agricultural and Food Chemistry, 50, 4796-4802.

Ng RC, Kassim NK, Yeap YSY, Ee GCL, Yazan SL, Musa KH. (2018). Isolation of carbazole alkaloids and coumarins from Aegle marmelos and Murraya koenigii and their antioxidant properties. Sains Malaysiana, 47(8), 1749-1756.

Osman FNA, Mohd Nor SM, Nafiah MA. (2021). Cytotoxicity effect of natural and synthetic girinimbines and their derivatives against human lung cancer cell lines A549. Malaysian Journal of Analytical Sciences, 25(6), 1020-1031.

Pei C, He Q, Liang S, Gong X. (2018). Mahanimbine exerts anticancer effects on human pancreatic cancer cells by triggering cell cycle arrest, apoptosis, and modulation of AKT/mammalian target of rapamycin (mTOR) and signal transducer and activator of transcription 3 (STAT3) signalling pathways. Medical Science Monitor, 24, 6975-6983.

Ramsewak RS, Nair MG, Strasburg GM, DeWitt DL, Nitiss JL. (1999). Biologically active carbazole alkaloids from Murraya koenigii. Journal of Agricultural and Food Chemistry, 47(2), 444-447.

Rao LJM, Ramalakshmi K, Borse BB, Raghavan B. (2006). Chemical composition of volatiles from coconut sap neera and effect of processing. Food Chemistry, 100, 742-747.

Sakunpak A, Saingam W, Jaisamut, S, Issuriya A, Ruangrungsi N. (2021). Pyranocarbazole alkaloids, isolated from Clausena cambodiana leaves, as a pancreatic cholesterol esterase inhibitor, and their HPLC–DAD quantitative determination method. Chemistry Papers, 75, 2451-2458.

Sim KM, Teh HM. (2011). A new carbazole alkaloid from the leaves of Malayan Murraya koenigii. Journal of Asian Natural Products Research, 13(10), 972-975.

Sukari MA, Mohd Noor HS, Abu Bakar NH, Ee GCL, Ismail IS, Rahmani M, Abdul AB. (2013). Larvicidal carbazole alkaloids from Murraya koenigii against dengue fever mosquito Aedes aegypti Linnaeus. Asian Journal of Chemistry, 25(14), 7719-7721.

Tan SP, Nafiah MA, Ahmad K. (2014). C23-carbazole alkaloids from Malayan Murraya koenigii (L.) Spreng. Journal of Chemical and Pharmaceutical Research, 6(4), 1093-1098.

Tan SP, Nafiah MA. (2021). A simple BF3•Et2O-mediated cycloaddition reaction to the formation of cyclic monoterpenoid pyrano[3,2-a]carbazole alkaloids. Letters in Organic Chemistry, 18(5), 395-399.

Wu TS, Wang ML, Wu PL, Ito C, Furukawa H. (1996). Carbazole alkaloids from the leaves of Murraya euchrestifolia. Phytochemistry, 41, 1433-1435.

Xie H, Zhang T, Yang N, Li Z, Liu Y. (2020). Anticancer effects of mahanimbine alkaloid on the human bladder cancer cells are due to the induction of G0/G1 cell cycle arrest, apoptosis and autophagy. Journal of B.U.ON.: Official Journal of the Balkan Union of Oncology, 25(2), 1166-1171.

Yedukondalu N, Thakur V, Mohmmed A, Gupta VK, Ali A. (2017). POCl3-mediated cyclization of (+)-S-mahanimbine led to the divergent synthesis of natural product derivatives with antiplasmodial activity. New Journal of Chemistry, 41(12), 4923-4930.

Yedukondalu N, Gupta G, Nadkarni JR, Gupta VK, Syed SH, Ali A. (2016). Divergent synthesis of prenylated carbazole alkaloid (+)-S-mahanimbine led to the discovery of a notch activator. RSC Advance, 6, 83069-83077.




How to Cite

Mohd Yunos, N., Mohd Nor, S. M., & Nafiah, M. A. (2024). Semi-synthesis of N-substituted Mahanimbine via Alkylation. Journal of Science and Mathematics Letters, 12(1), 34–42.